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WO2013031603A1 - Composé à cristaux liquides, son procédé de fabrication, composition de cristaux liquides, et élément électro-optique à cristaux liquides - Google Patents

Composé à cristaux liquides, son procédé de fabrication, composition de cristaux liquides, et élément électro-optique à cristaux liquides Download PDF

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Publication number
WO2013031603A1
WO2013031603A1 PCT/JP2012/071211 JP2012071211W WO2013031603A1 WO 2013031603 A1 WO2013031603 A1 WO 2013031603A1 JP 2012071211 W JP2012071211 W JP 2012071211W WO 2013031603 A1 WO2013031603 A1 WO 2013031603A1
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group
compound
substituted
atom
liquid crystal
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Japanese (ja)
Inventor
健史 北
横山　健二
渭原　聡
智之 淺井
英昌 高
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AGC Seimi Chemical Ltd
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AGC Seimi Chemical Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0462—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2CF2O- chain

Definitions

  • the present invention relates to a liquid crystal compound and a production method thereof, a liquid crystal composition containing the compound, and a liquid crystal electro-optical element.
  • Liquid crystal electro-optical elements include mobile devices such as mobile phones and PDAs, display devices for OA devices such as copiers and personal computer monitors, display devices for home appliances such as liquid crystal televisions, clocks, calculators, measuring instruments, and automotive instruments. It is used for a wide range of applications such as cameras. For this reason, the liquid crystal electro-optical element is required to have various performances such as a wide operating temperature range, a low operating voltage, high-speed response, and chemical stability. Since it is difficult to satisfy all the performances required for such a liquid crystal electro-optical element with a single compound, a liquid crystal compound and a non-liquid crystal compound having particularly excellent characteristics are usually used. Several combined liquid crystal compositions are used as a material exhibiting a liquid crystal phase used in a liquid crystal electro-optical element.
  • the compounds used in the above liquid crystal composition it has excellent compatibility with other liquid crystal compounds and non-liquid crystal compounds, is chemically stable, and has a wide temperature range when used in liquid crystal electro-optical elements. It is important to have a high-speed response and a low voltage drive.
  • compounds capable of exhibiting such properties compounds containing a linking group having a specific structure in the molecule, such as —CF 2 CF 2 — (see Patent Documents 1 and 2), —CF 2 O— (Patent Document 3). And compounds containing a linking group such as —CH 2 CH 2 CF 2 O— (see Patent Document 3) are known.
  • the group may be decomposed in some cases.
  • a liquid crystal compound that can further respond to a high demand for a liquid crystal electro-optical element is desired.
  • the present invention is chemically stable, excellent in compatibility with other liquid crystal materials or non-liquid crystal materials, and has a high responsiveness, low viscosity, and a wide liquid crystal temperature range by designing a bonding group to the linking group.
  • An object of the present invention is to provide a liquid crystal compound that can also have characteristics such as a high clearing point.
  • the present invention also provides a method for producing such a liquid crystal compound, a liquid crystal composition suitable for obtaining a highly reliable liquid crystal electro-optical element, and a liquid crystal electro-optical element using the liquid crystal composition. Objective.
  • the present invention provides a liquid crystal compound having a specific structure containing a novel linking group —CF 2 CF 2 CF 2 O— as the liquid crystal compound as described above.
  • the liquid crystal compound according to the present invention is represented by the following formula (1).
  • the symbol in Formula (1) shows the following meanings.
  • R 1 and R 2 are each independently a hydrogen atom, a halogen atom, —CN, —NCS, —SF 5 or an alkyl group having 1 to 18 carbon atoms, and one or more hydrogen atoms in the alkyl group May be substituted with a halogen atom, and an etheric oxygen atom (—O—) or a thioetheric sulfur atom (—S—) is inserted between the carbon-carbon atom (C—C) or at the bond terminal of the group.
  • One or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH— or —C ⁇ C—.
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 and A 7 Independently of each other, trans-1,4-cyclohexylene group, 1,4-cyclohexenylene group, 1,3 -Cyclobutylene group, 1,2-cyclopropylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group Or a 1,4-phenylene group, and in each of these groups, one or more hydrogen atoms may be substituted with a halogen atom, and one or two ⁇ CH— may be substituted with a nitrogen atom One or two —CH 2 — may be substituted with —O— or —S—.
  • Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently a single bond or an alkylene group having 1 to 4 carbon atoms, in which one or more hydrogen atoms are fluorine atoms
  • One or more —CH 2 — may be substituted with —O— or —S—, and one or more —CH 2 CH 2 — may be —CH ⁇ CH— or —C ⁇ C— may be substituted, and one —CH 2 CH 2 — may be substituted with —COO— or —OCO—.
  • m, n, p, q and r 0 or 1 independently of each other. However, 0 ⁇ m + n + p + q + r ⁇ 3.
  • the above -O- and / or -S- are not linked in the compound structure.
  • the liquid crystal compound is preferably represented by the following formula (1-1).
  • R 11 and R 21 are each independently a fluorine atom, —CN, or an alkyl group having 1 to 18 carbon atoms, wherein one or more hydrogen atoms may be substituted with a fluorine atom.
  • —O— or —S— may be inserted between C—C or at the bonding terminal of the group, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a 11 , A 21 , A 31 , A 41 , A 51 , A 61 and A 71 each independently a trans-1,4-cyclohexylene group or a 1,4-phenylene group,
  • one or more hydrogen atoms may be substituted with a halogen atom
  • one or two ⁇ CH— may be substituted with a nitrogen atom
  • one or two —CH 2 — is — It may be substituted with O— or —S—.
  • Z 11 , Z 21 , Z 31 , Z 41 and Z 51 are each independently a single bond, —COO—, —OCO—, —C ⁇ C— or an alkylene group having 1 to 4 carbon atoms, In the alkylene group, one or more hydrogen atoms may be substituted with a fluorine atom, and one or more —CH 2 — may be substituted with —O—.
  • m, n, p, q and r have the same meaning as described above.
  • the liquid crystal compound is more preferably represented by the following formula (1-2).
  • R 12 is an alkyl group having 1 to 10 carbon atoms, and one or more hydrogen atoms in the group may be substituted with a fluorine atom, and —O— is present between C—C or at the bond terminal of the group.
  • R 22 is a fluorine atom, —CN, or an alkyl group having 1 to 10 carbon atoms, and one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, —O— may be inserted at the bonding terminal, and one or more —CH 2 CH 2 — may be substituted with —CH ⁇ CH—.
  • a 12 , A 22 , A 32 , A 42 , A 52 , A 62 and A 72 independently of each other, a trans-1,4-cyclohexylene group, a 1,4-phenylene group or one or two of them 1,4-phenylene group in which a hydrogen atom is substituted with a fluorine atom.
  • Z 12 , Z 22 , Z 32 , Z 42 and Z 52 independently of each other, a single bond, —C 2 H 4 —, —COO—, —OCO—, —C ⁇ C—.
  • m, n, p, q and r have the same meaning as described above.
  • the following method can be provided as an example of a method for producing the liquid crystal compound as described above.
  • R 3 is —OR a , —N (R a ) (R b ), and R a and R b are each independently an alkyl group having 1 to 5 carbon atoms.
  • M a metal atom or a group containing a metal atom.
  • Other symbols have the same meaning as the symbols in the above formula (1).
  • the liquid crystal compound is a compound represented by the following formula (1 ′) in which A 4 in the above formula (1) is a 1,4-cyclohexylene group
  • the following method is used.
  • R 3 —OR a , —N (R a ) (R b ), and R a and R b are each independently an alkyl group having 1 to 5 carbon atoms.
  • M a metal atom or a group containing a metal atom.
  • -Ph- 1,4-phenylene group.
  • -Cy- trans-1,4-cyclohexylene group.
  • Other symbols have the same meaning as the symbols in the above formula (1).
  • the present invention also provides a liquid crystal composition comprising the liquid crystal compound represented by the formula (1).
  • the present invention also provides a liquid crystal electro-optical element formed by sealing the liquid crystal composition between two substrates provided with electrodes.
  • the liquid crystal compound represented by the formula (1) of the present invention is chemically stable and excellent in compatibility with other liquid crystal materials or non-liquid crystal materials.
  • the liquid crystal compound of the present invention has a viscosity equal to or lower than that of a liquid crystal compound having a similar structure except for a linking group.
  • the compound of the present invention has various performances required for the liquid crystal electro-optic element, specifically, for example, a wide operating temperature by appropriately selecting the ring group, substituent and linking group constituting the compound.
  • a liquid crystal composition satisfying the range, high-speed response, chemical stability, and the like can be prepared.
  • an element excellent in high-speed response can be obtained in a wide temperature range.
  • a compound having a —CF 2 CF 2 CF 2 O— linking group is highly versatile and can be easily and efficiently produced industrially easily.
  • liquid crystal compound represented by the formula (1) is referred to as a compound (1), and the compounds represented by other formulas are also described in the same manner.
  • a liquid crystal compound means a compound that exhibits a liquid crystal phase and a compound that does not exhibit a liquid crystal phase but is useful as a constituent of a liquid crystal composition.
  • the one closer to R 1 in the formula (1) is always the first place, and the one closer to R 2 is always the fourth place.
  • “ ⁇ is negatively large” means that ⁇ is negative and the absolute value thereof is large. That is, if the value of ⁇ is ⁇ 1 and ⁇ 2, -2 is “ ⁇ is negatively larger”.
  • the liquid crystal electro-optical element is not limited to a display element, but various functional elements that use the electrical or optical characteristics of liquid crystal, such as a liquid crystal display element, a light control window, and an optical shutter. And elements used for applications such as a polarization conversion element and a variable focus lens.
  • examples of the group in which one or more hydrogen atoms in the alkyl group are substituted with halogen atoms include a fluoroalkyl group, A chloroalkyl group etc. are mentioned.
  • a fluorine atom is preferable.
  • examples of the group in which —O— or —S— is inserted between C—C in the alkyl group include an alkoxyalkyl group or an alkylthioalkyl group, and —O— or —S— is inserted at the bond terminal of the group.
  • Examples of the group include an alkoxy group and an alkylthio group.
  • Examples of the group in which —CH 2 CH 2 — in the alkyl group is substituted with —CH ⁇ CH— or —C ⁇ C— include an alkenyl group and an alkynyl group.
  • substitution with — or —C ⁇ C— may be performed simultaneously on the same alkyl group.
  • Examples of the group in which substitution of a fluorine atom and insertion of —O— are simultaneously performed include a fluoroalkoxy group and a fluoroalkoxyalkyl group.
  • Examples of the group in which —CH ⁇ CH— or —C ⁇ C— substitution and fluorine atom substitution are simultaneously performed include a fluoroalkenyl group and a fluoroalkynyl group.
  • Examples of the group in which substitution of —CH ⁇ CH— or —C ⁇ C— and insertion of —O— or —S— between C—C are performed simultaneously include alkenyloxyalkyl group, alkynyloxyalkyl group, alkenyl A thioalkyl group and an alkynylthioalkyl group can be mentioned.
  • Examples of the group in which —CH ⁇ CH— or —C ⁇ C— is substituted and —O— or —S— is inserted at the bonding end of the group include an alkenyloxy group, an alkynyloxy group, an alkenylthio group, and an alkynylthio group.
  • Groups. Further, groups in which fluorine atom substitution, —CH ⁇ CH— or —C ⁇ C— substitution, and —O— or —S— insertion are performed simultaneously include fluoroalkenyloxy group, fluoroalkynyloxy group And a fluoroalkenylthio group. These groups may be either linear or branched, but are preferably linear.
  • R 1 and R 2 are preferably fluorine atoms, —CN, and groups having 1 to 18 carbon atoms, since reactivity and side reactions are unlikely to occur.
  • R 1 is particularly preferably an alkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkenyloxy group, or alkenyloxyalkyl group having 1 to 10 carbon atoms.
  • R 2 is a fluorine atom, —CN, and an alkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkenyloxy group, alkenyloxyalkyl group, fluoroalkyl group, fluoroalkoxy group having 1 to 10 carbon atoms, A fluoroalkoxyalkyl group is particularly preferred.
  • substitution of a hydrogen atom with a halogen atom, ⁇ CH—nitrogen may be performed simultaneously on the same group.
  • a halogen atom a chlorine atom or a fluorine atom is preferable.
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 and A 7 are 1,4-phenylene groups and further have a halogen atom as a substituent, one 1,4-phenylene group is substituted.
  • the number of halogen atoms to be used is 1 to 4, but 1 or 2 is preferable among them.
  • the number of halogen atoms is preferably 1 to 4.
  • the halogen atom may be bonded to the 1st or 4th carbon atom of the trans-1,4-cyclohexylene group.
  • Examples of the group in which one or two ⁇ CH— in the 1,4-phenylene group are substituted with a nitrogen atom include a 2,5-pyrimidinylene group and a 2,5-pyridinylene group.
  • Examples of the group in which one or two —CH 2 — in the trans-1,4-cyclohexylene group is substituted with —O— or —S— include a 1,3-dioxane-2,5-diyl group, A 1,3-dithian-2,5-diyl group may be mentioned.
  • a 1,4-phenylene group substituted with at least one of a halogen atom and a nitrogen atom is referred to as a “substituted 1,4-phenylene group” and substituted with at least one of a halogen atom, —O— and —S—.
  • the 1,4-cyclohexylene group thus prepared is referred to as “substituted trans-1,4-cyclohexylene group”.
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 and A 7 are trans-1,4-cyclohexylene group, 1, A 4-phenylene group, a substituted trans-1,4-cyclohexylene group, or a substituted 1,4-phenylene group is preferred.
  • a trans-1,4-cyclohexylene group, a 1,4-phenylene group, or a 1,4-phenylene group in which one or two hydrogen atoms in the group are substituted with a fluorine atom is particularly preferable.
  • a 4 is a trans-1,4-cyclohexylene group.
  • a 4 is a 1,4-phenylene group, or a 1,4-phenylene group in which one or two hydrogen atoms in the group are substituted with fluorine atoms. It is particularly preferred.
  • the one closer to R 1 in the formula (1) is the first and the one closer to R 2 is the fourth And
  • Z 1 , Z 2 , Z 3 , Z 4 and Z 5 have the same meaning as described above.
  • substitution of a hydrogen atom with a fluorine atom substitution of —CH 2 — with —O— or —S—, —CH ⁇ CH— of —CH 2 CH 2 —, —C ⁇ C—, —COO— , —OCO— may be substituted simultaneously for the same group.
  • alkylene group in which one or more hydrogen atoms in the group are substituted with fluorine atoms examples include —CF 2 CF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CHFCH 2 —, —CH 2 CHF—, —CF 2 CHF—, —CHFCF 2 — and the like can be mentioned.
  • alkylene group in which one or more —CH 2 — in the group is substituted by —O— or —S— include —CH 2 O—, —OCH 2 —, —CH 2 S—, —SCH 2 — and the like. Is mentioned.
  • examples of the group in which substitution of a hydrogen atom in a group with a fluorine atom and substitution of —CH 2 — in the group with —O— are performed simultaneously include —CF 2 O—, —OCF 2 — Etc.
  • the alkylene group in which one or more —CH 2 CH 2 — in the group is substituted with —CH ⁇ CH— or —C ⁇ C— includes an alkenylene group or an alkynylene group.
  • the alkenylene group or alkynylene group includes —CH ⁇ CH—, —CH ⁇ CH—CH 2 —, —CH ⁇ CH—CH 2 —CH 2 —, —CH ⁇ CH—CH ⁇ CH—, —CH 2 —CH.
  • ⁇ CH—CH 2 —, —C ⁇ C—, —C ⁇ C—CH 2 —, —C ⁇ C—CH 2 —CH 2 —, —C ⁇ C—C ⁇ C—, —CH 2 —C ⁇ C—CH 2 — and the like can be mentioned. Further, double bonds and triple bonds may be mixed as in —CH ⁇ CH—C ⁇ C—. These groups may be reversed. Examples of groups in which —CH ⁇ CH— or —C ⁇ C— and fluorine atoms are simultaneously substituted include —CF ⁇ CF—, —CF ⁇ CF—C ⁇ C— and the like.
  • Examples of the group in which one —CH 2 CH 2 — is substituted with —COO— or —OCO— include —COO—, —OCO—, —CH 2 CH 2 —COO—, —CH 2 CH 2 -OCO- and the like.
  • Z 1 , Z 2 , Z 3 , Z 4 or Z 5 in the formula (1) defined above is a single bond, the groups present on both sides of each group must be directly bonded. Means. For example, when Z 1 is a single bond and m and n are 1, A 1 and A 2 are directly bonded. When Z 1 , Z 2 and Z 3 are single bonds and m, n and p are 0, R 1 and A 4 are directly bonded. The same applies to Z 2 , Z 3 , Z 4 and Z 5 .
  • Z 1 , Z 2 , Z 3 , Z 4, and Z 5 are each a single bond, —COO—, —OCO—, —C ⁇ C— or an alkylene group having 1 to 4 carbon atoms for ease of synthesis or the like.
  • One or more hydrogen atoms in the group may be substituted with a fluorine atom, and one or more —CH 2 — in the group may be substituted with —O—.
  • a single bond, —C 2 H 4 —, —COO—, —OCO— or —C ⁇ C— is particularly preferable.
  • m, n, p, q and r have the same meaning as described above.
  • m, n, p, q, and r can be suitably selected according to the characteristics required for the compound. For example, when importance is attached to the low viscosity of the compound (1) or the excellent compatibility of the compound with other liquid crystal materials or non-liquid crystal materials, it is preferable that 0 ⁇ m + n + p + q + r ⁇ 1. On the other hand, when emphasizing the high liquid crystal temperature range of the compound, it is preferable that 1 ⁇ m + n + p + q + r ⁇ 3.
  • R —R 2 is preferably an electron withdrawing group.
  • R 2 fluorine atom, —OCF 3 , —OCF 2 H, —CN, —NCS, or —SF 5
  • a 5 , A 6 , A 7 Independently of each other, 1,4-phenylene group, 3-fluoro-1,4-phenylene group, or 3,5-difluoro-1,4-phenylene group.
  • Z 4 , Z 5 single bond q, r: independently of each other 0 or 1
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 and A 7 are 2,3-difluoro-1,4- A phenylene group is preferred.
  • R 1 and R 2 directly bonded to the 2,3-difluoro-1,4-phenylene group are preferably alkoxy groups.
  • a 1,4-phenylene group when a 1,4-phenylene group is substituted on the carbon atom side of —CF 2 O—, if the group is not substituted with a fluorine atom, The CF 2 O— linking group is unstable and may be converted to —COO— by hydrolysis.
  • the linking group in the compound having the —CF 2 CF 2 CF 2 O— linking group of the present invention, the linking group may be substituted with a 1,4-phenylene group not substituted with a fluorine atom.
  • the compound having a —CF 2 CF 2 CF 2 O— linking group of the present invention is not limited even if the structure of the ring group at both ends of the linking group is not limited to a fluorine-substituted 1,4-phenylene group or the like. It can be seen that it has a feature that can be obtained stably.
  • the compound (1-1) is preferable.
  • R 11 - (A 11) m -Z 11 - (A 21) n -Z 21 - (A 31) p -Z 31 -A 41 -CF 2 CF 2 CF 2 OA 51 -Z 41 - (A 61) q -Z 51 - (A 71) r -R 21 (1-1) The symbols in the formula are as described above.
  • the compound (1-2) is more preferred.
  • the symbols in the formula are as described above.
  • Preferable examples of compound (1) include the following compounds.
  • R 12 and R 22 have the same meaning as described above, and other symbols have the following meanings.
  • -Cy- trans-1,4-cyclohexylene group.
  • -Phe- 1,4-phenylene group optionally substituted by one or two fluorine atoms.
  • R 3 is —OR a , —N (R a ) (R b ), and R a and R b are each independently an alkyl group having 1 to 5 carbon atoms.
  • M a metal atom or a group containing a metal atom.
  • Other symbols have the same meaning as the symbols in the above formula (1).
  • a series of reactions for obtaining the compound (1) by the production method 1 can be expressed as follows.
  • R 3 of the compound (9) is preferably —OR a because synthesis is easy.
  • R a is preferably an alkyl group having 1 to 3 carbon atoms.
  • Compound (10) can be synthesized, for example, by the following method.
  • the symbols in the formula have the same meaning as described above.
  • X is preferably a chlorine atom, a bromine atom or an iodine atom because of good reactivity, and an iodine atom is particularly preferred.
  • Examples of the metalation reaction of compound (11) include lithiation and a method of using a Grignard reagent by reaction with metallic magnesium.
  • Examples of lithiation include a method using metallic lithium and a halogen-metal exchange reaction using alkyllithium such as n-butyllithium as a lithiating agent.
  • M of the compound (10) obtained by metalation of the compound (11) MgI, MgBr, MgCl and Li are preferable, and Li is particularly preferable.
  • the compound (10) obtained by metalation of the compound (11) may be isolated and then reacted with the compound (9) without isolation after the metalation reaction. You may make it react with a compound (9) continuously.
  • the amount of compound (10) to be used is preferably 0.9 to 2.0 moles per 1 mole of compound (9). More preferred is .5 moles.
  • the amount of the compound (11) used is 0.9-2. 0 mol is preferable, and 1 to 1.5 mol is more preferable.
  • solvents include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; tetrahydrofuran, diethyl ether, diisopropyl ether, dibutyl ether, and t-butylmethyl.
  • Ether solvents such as ether and dimethoxyethane; petroleum ethers or a suitable mixed solvent of the above solvents can be used.
  • ether solvents such as diethyl ether and t-butyl methyl ether, and mixed solvents of ether solvents and aliphatic hydrocarbon solvents are preferable.
  • the reaction temperature is preferably ⁇ 100 to 50 ° C., more preferably ⁇ 95 to ⁇ 80 ° C.
  • the reaction time is preferably 0.1 to 24 hours, more preferably 0.1 to 5 hours.
  • fluorination of compound (8) is preferably carried out in a solvent.
  • Solvents that can be used include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; ethyl acetate, methyl acetate, propyl acetate, and the like Ester solvents such as methanol and ethanol; ketone solvents such as acetone and methyl ethyl ketone; ether solvents such as tetrahydrofuran, diethyl ether, dibutyl ether, t-butyl methyl ether, and dimethoxyethane; dichloromethane, 1,2 -Chlorinated solvents such as dichloroethane; petroleum ethers or a suitable mixed solvent of the above-mentioned solvents
  • Fluorination reaction includes sulfur tetrafluoride, N, N-diethylaminosulfur trifluoride, morpholino sulfur trifluoride, bis- (2-dimethoxyethyl) aminosulfur trifluoride, or carbonyl using xenon difluoride Examples thereof include direct fluorination reaction of compounds and oxidative desulfurization fluorination reaction via ortho-thioester, dithiane, and thiocarbonyl. Among these, reaction using N, N-diethylaminosulfur trifluoride is more preferable.
  • the amount of the fluorinating reagent to be used is preferably 0.5 to 20 times, more preferably 1 to 5 times, based on 1 mol of Compound (8).
  • the reaction temperature is preferably 0 to 150 ° C, more preferably 20 to 80 ° C.
  • the reaction time is preferably 1 to 72 hours, more preferably 3 to 24 hours.
  • R 3 —OR a , —N (R a ) (R b ), and R a and R b are each independently an alkyl group having 1 to 5 carbon atoms.
  • M a metal atom or a group containing a metal atom.
  • -Ph- 1,4-phenylene group.
  • -Cy- trans-1,4-cyclohexylene group.
  • Other symbols have the same meaning as the symbols in the above formula (1).
  • a series of reactions for obtaining the compound (1 ′) by the production method 2 can be expressed as follows.
  • -Ch- is a 1,4-cyclohexenylene group, and the definitions and preferred embodiments of other symbols are as described above for the compounds (1) and (1 ').
  • a compound (9 ') can be obtained by the method similar to the compound (9) of the manufacturing method 1.
  • R 4 may be a group usually used in organic synthesis as a protective group for the OH group.
  • a benzyl group, an acyl group, etc. are mentioned, and since it is easy to synthesize, a benzyl group is preferable.
  • the step of obtaining the compound (8 ′) from the compound (11) is the same as the step of obtaining the compound (8) by the production method 1.
  • the fluorination of the compound (8 ′) is the same as the step of obtaining the compound (1) by the production method 1.
  • the compound (7) obtained by fluorinating the compound (8 ′) is preferably hydrogenated to produce the compound (6) in a solvent.
  • Solvents that can be used in the production of compound (6) include aromatic hydrocarbon solvents such as benzene, toluene, xylene and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane and octane; acetic acid Ester solvents such as ethyl, methyl acetate and propyl acetate; alcohol solvents such as methanol and ethanol; ketone solvents such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran, diethyl ether, dibutyl ether, t-butyl methyl ether and dimethoxyethane System solvents; petroleum ethers or an appropriate mixed solvent of the above solvents can be used.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene and ethylbenzene, aliphatic hydrocarbon solvents
  • the production of compound (6) is preferably carried out in the presence of a heterogeneous catalyst.
  • the catalyst that can be used in the production of the compound (6) include transition metals such as palladium carbon, rhodium carbon, ruthenium carbon, Raney nickel, and platinum oxide.
  • the amount of the catalyst used is preferably 0.01 to 1.0 times, more preferably 0.1 to 0.5 times the mass of the compound (7).
  • the reaction temperature is preferably ⁇ 50 to 100 ° C., more preferably 0 to 40 ° C.
  • the reaction time is preferably 0.1 to 24 hours, more preferably 0.1 to 3 hours.
  • the oxidation reaction for producing compound (5) by oxidizing compound (6) includes Dess-Martin oxidation reaction using organic hypervalent iodine reagent, Jones oxidation using pyridinium chlorochromate and pyridinium dichromate. Reaction, Opppenauer oxidation reaction using tetraisopropoxyaluminum and acetone, Swern oxidation reaction using dimethyl sulfoxide and oxalyl chloride, or oxidation reaction using acetic acid and sodium hypochlorite aqueous solution. Among these, acetic acid, hypochlorous acid An oxidation reaction using an aqueous sodium acid solution is particularly desired.
  • the amount of acetic acid used is preferably 1 to 30 times, more preferably 3 to 5 times the mass of the compound (6).
  • the sodium hypochlorite aqueous solution is preferably used in an amount of 0.1 to 5 times, more preferably 0.1 to 1 times the amount of the compound (6).
  • the reaction temperature is preferably 0 to 100 ° C, more preferably 20 to 60 ° C.
  • the reaction time is preferably 1 to 72 hours, more preferably 3 to 48 hours.
  • Solvents include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; tetrahydrofuran, diethyl ether, diisopropyl ether, dibutyl ether, and t-butylmethyl.
  • Ether solvents such as ether and dimethoxyethane; petroleum ethers or a suitable mixed solvent of the above solvents can be used.
  • ether solvents such as diethyl ether and t-butyl methyl ether, and mixed solvents of ether solvents are preferable.
  • the amount of compound (4) to be used is preferably 0.9 to 20.0 mol, more preferably 1 to 10 mol, per 1 mol of compound (5).
  • the reaction temperature is preferably ⁇ 70 to 50 ° C., more preferably ⁇ 10 to 30 ° C.
  • the reaction time is preferably 0.1 to 24 hours, more preferably 0.1 to 5 hours.
  • the compound (4) can be easily obtained by a method described in a book of organic synthesis such as a new experimental chemistry course (published by Maruzen Co., Ltd.).
  • M is a metal atom or a group containing a metal atom.
  • MgI, MgBr, MgCl, and Li are especially preferable.
  • the compound (4) may be reacted with the compound (5) after isolation, or may be continuously reacted with the compound (5) without isolation after the metalation reaction.
  • the compound (2) is obtained by dehydrating the compound (3) obtained by the reaction between the compound (4) and the compound (5).
  • the dehydration reaction is preferably performed under acidic conditions.
  • the dehydration reaction is preferably carried out in a solvent, and examples of the solvent include those exemplified in the above reaction. Among them, aromatic hydrocarbon solvents such as toluene, ether solvents such as tetrahydrofuran, and mixtures of these solvents A solvent is preferred.
  • acids that can be used in the dehydration reaction include strong acids such as hydrochloric acid and sulfuric acid; carboxylic acids such as trifluoroacetic acid, acetic acid, and formic acid; and organic acids such as paratoluenesulfonic acid.
  • the amount of the acid used is preferably 0.01 to 10 equivalents, more preferably 0.1 to 1 equivalents, relative to compound (2).
  • the reaction temperature is preferably 0 ° C. to reflux, more preferably 30 ° C. to reflux.
  • the reaction time is preferably 0.1 to 24 hours, more preferably 0.1 to 3 hours.
  • the compound (1 ′) can be obtained by hydrogenating the compound (2).
  • the hydrogenation reaction is preferably carried out in a solvent, and examples of the solvent include those exemplified in the above reaction. Among them, alcohol solvents such as ethanol, ester solvents such as ethyl acetate, Mixed solvents are preferred.
  • the synthesis of compound (1 ′) is preferably carried out in the presence of a heterogeneous catalyst.
  • the catalyst that can be used in the production of the compound (1 ′) include transition metals such as palladium carbon, rhodium carbon, ruthenium carbon, Raney nickel, and platinum oxide.
  • the amount of the catalyst used is preferably 0.01 to 1.0 times, more preferably 0.1 to 0.5 times the mass of the compound (2).
  • the reaction temperature is preferably 0-100 ° C, more preferably 30-80 ° C.
  • the reaction time is preferably 0.1 to 24 hours, more preferably 0.1 to 3 hours.
  • the present invention provides a liquid crystal composition comprising the compound (1) of the present invention.
  • This liquid crystal composition is constituted by mixing the compound (1) of the present invention with other liquid crystal compounds or non-liquid crystal compounds (collectively referred to as “other compounds”).
  • the content of the compound (1) in the liquid crystal composition of the present invention can be appropriately changed depending on the purpose of use, the purpose of use, the type of other compounds, etc. 5 to 50% by mass is preferable, and 2 to 20% by mass is particularly preferable. Moreover, you may contain 2 or more types of compounds (1) in a liquid-crystal composition by a use, a use purpose, etc. In that case, the total amount of the compound (1) is preferably 0.5 to 80% by mass, particularly 2 to 50% by mass, based on the total amount of the liquid crystal composition.
  • Other compounds used in combination with the compound (1) include components for adjusting the refractive index anisotropy value, components for reducing the viscosity, components exhibiting liquid crystallinity at low temperatures, components for improving the dielectric anisotropy, and cholesteric A component for imparting properties, a component exhibiting dichroism, a component for imparting conductivity, and various other additives. These are appropriately selected depending on the application, required performance and the like, but usually those composed of a liquid crystal compound, a main component having a similar structure to the liquid crystal compound, and an additive component added if necessary.
  • examples of the other compound include those represented by the following formulae.
  • R 5 and R 6 represent a group such as an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a halogen atom or a cyano group.
  • R 3 and R 4 may be the same or different from each other.
  • -Cy- represents a trans-1,4-cyclohexylene group
  • -Ph- represents a 1,4-phenylene group
  • -PhFF- represents a difluorophenylene group.
  • a hydrogen atom present in a ring structure or a terminal group in the compound may be substituted with a halogen atom, a cyano group, a methyl group, or the like.
  • the cyclohexane ring or the benzene ring may be substituted with another 6-membered ring or 5-membered ring, for example, a pyrimidine ring or a dioxane ring.
  • liquid crystal composition of the present invention examples include the following.
  • the symbols in the formula have the same meaning as described above.
  • the present invention provides a liquid crystal electro-optical element that uses the liquid crystal composition as a constituent material of a liquid crystal layer.
  • a liquid crystal electro-optical element having an electro-optical element portion formed by sandwiching a liquid crystal layer formed by injecting the liquid crystal composition of the present invention into a liquid crystal cell or the like between two substrates provided with electrodes.
  • This liquid crystal electro-optic element has various modes such as TN mode, STN mode, ECB mode, VA mode, guest host mode, dynamic scattering mode, phase change mode, DAP mode, dual frequency drive mode, ferroelectric liquid crystal display mode, etc.
  • the one driven by is mentioned.
  • As a drive mode passive drive and active drive can be used.
  • a typical liquid crystal electro-optic element includes a twisted nematic (TN) type liquid crystal display element.
  • the twisted nematic (TN) type liquid crystal display device first, plastics, onto a substrate such as glass, of SiO 2, Al 2 O undercoat layer or a color filter layer, such as 3 to form optionally, an In 2 O
  • a film made of 3- SnO 2 (ITO), SnO 2 or the like is formed, and an electrode having a required pattern is formed by photolithography or the like.
  • an overcoat layer of polyimide, polyamide, SiO 2 , Al 2 O 3 or the like is formed and oriented.
  • a sealing material is printed on this, it arrange
  • composition of the present invention is injected into an empty cell, and the injection port is sealed with a sealant to form a liquid crystal cell.
  • this liquid crystal cell is laminated with a polarizing plate, a color polarizing plate, a light source, a color filter, a transflective plate, a reflecting plate, a light guide plate, an ultraviolet cut filter, etc., printing characters, figures, etc., non-glare processing, etc.
  • a liquid crystal electro-optical element can be obtained.
  • the above description describes the basic configuration and manufacturing method of the liquid crystal electro-optic element, and other configurations can be adopted.
  • a substrate using a two-layer electrode a two-layer liquid crystal cell having a two-layer liquid crystal layer, a substrate using a reflective electrode, an active matrix device using an active matrix substrate having an active element such as a TFT or MIM, etc.
  • Various configurations can be employed.
  • the composition of the present invention is also suitable for active matrix devices such as TFT and MIM.
  • composition of the present invention is a mode other than the TN type, that is, a high twist angle super twist nematic (STN) type liquid crystal electro-optical element or a guest-host (GH) type liquid crystal using a polychromatic dye.
  • 19 F-NMR and GC-MS data of the obtained compound (12a) are shown.
  • 19 F-NMR and GC-MS data of the obtained compound (11a) are shown.
  • 19 F-NMR and GC-MS data of the obtained compound (6a) are shown.
  • 19 F-NMR and GC-MS data of the obtained compound (3a) are shown.
  • 19 F-NMR and GC-MS data of the obtained compound (2a) are shown.
  • the clearing point (Tc) of compound (1a) was 95.8 ° C., and the refractive index anisotropy ( ⁇ n) was 0.082.
  • the shear viscosity at 25 ° C. was 10.6 mm 2 ⁇ s ⁇ 1 , and ⁇ was 7.4.
  • Each of the above physical properties was prepared by mixing 90% by mass of the liquid crystal composition “ZLI-4792” manufactured by Merck Co., Ltd. at a ratio of 10% by mass of the compound (1a) of the present invention. It measured with the following method using the composition.
  • [Measurement of liquid crystal clearing point (Tc)] Place the liquid crystal composition on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope, raise the temperature at 1 ° C./min, observe the phase change, measure the Tc of the liquid crystal composition, and extrapolate the measured value Thus, the extrapolated value of Tc of compound (1a) was calculated.
  • optical anisotropy (refractive index anisotropy; ⁇ n)
  • a voltage of 100 mV was applied to this cell at 20 ° C., and the dielectric constant ( ⁇ ) in the minor axis direction of the liquid crystal molecules was measured. A dielectric constant ( ⁇ ) in the major axis direction of liquid crystal molecules was measured by applying a voltage of 88V. The dielectric anisotropy ( ⁇ ) of the compound was determined by obtaining ⁇ of the composition from the formula ⁇ ⁇ and extrapolating.
  • 19 F-NMR and GC-MS data of the obtained compound (3b) are shown.
  • 19 F-NMR and GC-MS data of the obtained compound (2b) are shown.
  • the clearing point (Tc) of compound (1a) was 154.8 ° C., and the refractive index anisotropy ( ⁇ n) was 0.112.
  • the shear viscosity at 25 ° C. was 16.9 mm 2 ⁇ s ⁇ 1 , and ⁇ was 8.8.
  • Compound ( 1c) had a clearing point (Tc) of ⁇ 6.0 ° C. and a refractive index anisotropy ( ⁇ n) of 0.122.
  • the shear viscosity at 25 ° C. was 14.1 mm 2 ⁇ s ⁇ 1 , and ⁇ was 10.0.
  • Phase transition temperature C 38.2 I The extrapolated value was determined using Merck liquid crystal composition ZLI-4792 as the mother liquid crystal.
  • Compound (1d) had a clearing point (Tc) of ⁇ 49.7 ° C. and a refractive index anisotropy ( ⁇ n) of 0.109.
  • the shear viscosity at 25 ° C. was 19.5 mm 2 ⁇ s ⁇ 1 , and ⁇ was 15.5.
  • Phase transition temperature C 34.0 I When extrapolated values were determined using Merck's liquid crystal composition ZLI-4792 as the mother liquid crystal, the clearing point (Tc) of compound (1e) was ⁇ 11.7 ° C., and the refractive index anisotropy ( ⁇ n) was 0.076. The shear viscosity at 25 ° C. was 17.0 mm 2 ⁇ s ⁇ 1 , and ⁇ was 10.7.
  • the clearing point (Tc) of compound (1f) was 219.1 ° C.
  • the refractive index anisotropy ( ⁇ n) was 0.105
  • the shear viscosity at 25 ° C. was 29.8 mm 2 ⁇ s ⁇ 1
  • ⁇ was 7.9.
  • the extrapolated value was determined using Merck's liquid crystal composition ZLI-4792 as the mother liquid crystal.
  • the clearing point (Tc) of the compound (1g) was 171 ° C.
  • the refractive index anisotropy ( ⁇ n) was 0.162, 25 ° C.
  • the shear viscosity was 32.6 mm 2 ⁇ s ⁇ 1 , and ⁇ was 9.3.
  • -Ph ( 3F, 5F) — represents a 3,5-difluoro-1,4-phenylene group
  • —Ph (2F, 3F) — represents a 2,3-difluoro-1,4-phenylene group.
  • -Cy- and -Ph have the same meaning as described above.
  • the positions of the substituents corresponding to the cyclic groups A 1 to A 7 are based on the R 1 side being the 1st position and the R 2 side being the 4th position as described above. Specifically, the left side is the first place and the right side is the fourth place in the formula.
  • “C 3 H 7 —Cy—Cy—CF 2 CF 2 CF 2 O—Ph (3F, 5F) —F” is the compound (1a) of the above Example. The same applies to other substituents and other compounds.
  • Examples of compounds in which Z 1 to Z 5 are not a single bond include the following.
  • the compound (1a) of the present invention has a higher liquid crystal phase upper limit temperature and the widest liquid crystal temperature range as compared with the compound having the same structure of the portion other than the linking group. I found it.
  • a liquid crystal composition was prepared by mixing 90% by mass of a liquid crystal composition “ZLI-4792” manufactured by Merck Co. at a ratio of 10% by mass of the compound (1a) of the present invention.
  • This liquid crystal composition is referred to as composition (A).
  • a composition was prepared by mixing 90% by mass of “ZLI-4792” with each compound at a ratio of 10% by mass.
  • Table 4 shows physical property values of the compounds (1a), (C1), (C2), and (C3) obtained by using the composition.
  • Tc and shear viscosity were measured in the same manner as in the compound (1a) and obtained by extrapolation.
  • the compound (1a) of the present invention has a high Tc and a low viscosity as compared with a compound having the same structure except for the linking group.
  • composition (A) A composition was prepared by mixing 10% by mass of the compound (1a) with Merck liquid crystal composition ZLI-4792. This is designated as composition (A). Similarly, the composition which mixed 10 mass% of compound (1c) and compound (1e) was prepared, respectively. Let these be a composition (B) and a composition (C), respectively. Each of the compositions was sealed in a glass cell and irradiated with a xenon lamp for 9 hours. The degree of cis isomerization and decomposition of the sample was measured by measuring Tc of the composition after irradiation. The results are shown in Table 5.
  • Tc of the composition containing compound (1a), compound (1c) and compound (1e) hardly changed. From this, it was found that the compound (1a), the compound (1c) and the compound (1e) of the present invention have good light stability.
  • the fluorine-containing liquid crystal compound of the present invention has high Tc, a wide liquid crystal temperature range, low viscosity, high light stability, and does not cause precipitation even when added to the composition. It has been found that it has good compatibility with the compound. It was also found that ⁇ n and ⁇ had sufficient values to be used as constituent components of the liquid crystal composition. It has been clarified that the use of such a compound of the present invention for a liquid crystal composition makes it possible to prepare a liquid crystal composition having both high Tc and low viscosity.

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Abstract

Cette invention concerne : un composé à cristaux liquides qui peut combiner des caractéristiques telles que la stabilité chimique, une excellente compatibilité avec d'autres matériaux de type à cristaux liquides ou non, une réponse rapide, une basse viscosité, une large plage de températures de cristaux liquides et un point de compensation élevé ; un procédé de fabrication dudit composé ; une composition de cristaux liquides le contenant ; et un élément d'affichage à cristaux liquides. Le composé selon l'invention contient un groupe lié par -CF2CF2CF2O-, à savoir (1) R1-(A1)m-Z1-(A2)n-Z2-(A3)p-Z3-A4-CF2CF2CF2O-A5-Z4-(A6)q-Z5-(A7)r-R2.
PCT/JP2012/071211 2011-08-29 2012-08-22 Composé à cristaux liquides, son procédé de fabrication, composition de cristaux liquides, et élément électro-optique à cristaux liquides Ceased WO2013031603A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014157551A1 (fr) * 2013-03-29 2014-10-02 Ａｇｃセイミケミカル株式会社 Composé, procédé pour produire celui-ci, composition de cristaux liquides, et élément électro-optique à cristaux liquides
CN113795538A (zh) * 2019-05-10 2021-12-14 索尔维特殊聚合物意大利有限公司 含全氟环丁烷单体的制备方法
CN115745750A (zh) * 2022-09-28 2023-03-07 山东天隅新材料科技有限公司 邻苯基苯酚、制备方法及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4142519A1 (de) * 1991-01-31 1992-08-06 Merck Patent Gmbh Fluorbenzolderivate und fluessigkristallines medium
JPH07506368A (ja) * 1992-04-28 1995-07-13 ミネソタ　マイニング　アンド　マニュファクチャリング　カンパニー ペルフルオロエーテル末端部分を有する液晶化合物
JP2003002858A (ja) * 2000-08-10 2003-01-08 Chisso Corp ジフルオロプロピレンオキシ基を結合基とする液晶性化合物、液晶組成物および液晶表示素子
DE10335606A1 (de) * 2002-08-29 2004-03-11 Merck Patent Gmbh Flüssigkristalline Verbindungen mit CF2CF2O- oder CF2OCF2-Brücke
WO2009150963A1 (fr) * 2008-06-09 2009-12-17 チッソ株式会社 Composé pentacyclique cristal liquide contenant un cycle cyclohexane, composition de cristaux liquides et élément d’écran à cristaux liquides
WO2010047260A1 (fr) * 2008-10-21 2010-04-29 チッソ株式会社 Composé de cristal liquide pentacyclique présentant un hétérocycle contenant de l’azote, composition de cristaux liquides, et élément d’affichage à cristaux liquides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4142519A1 (de) * 1991-01-31 1992-08-06 Merck Patent Gmbh Fluorbenzolderivate und fluessigkristallines medium
JPH07506368A (ja) * 1992-04-28 1995-07-13 ミネソタ　マイニング　アンド　マニュファクチャリング　カンパニー ペルフルオロエーテル末端部分を有する液晶化合物
JP2003002858A (ja) * 2000-08-10 2003-01-08 Chisso Corp ジフルオロプロピレンオキシ基を結合基とする液晶性化合物、液晶組成物および液晶表示素子
DE10335606A1 (de) * 2002-08-29 2004-03-11 Merck Patent Gmbh Flüssigkristalline Verbindungen mit CF2CF2O- oder CF2OCF2-Brücke
WO2009150963A1 (fr) * 2008-06-09 2009-12-17 チッソ株式会社 Composé pentacyclique cristal liquide contenant un cycle cyclohexane, composition de cristaux liquides et élément d’écran à cristaux liquides
WO2010047260A1 (fr) * 2008-10-21 2010-04-29 チッソ株式会社 Composé de cristal liquide pentacyclique présentant un hétérocycle contenant de l’azote, composition de cristaux liquides, et élément d’affichage à cristaux liquides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014157551A1 (fr) * 2013-03-29 2014-10-02 Ａｇｃセイミケミカル株式会社 Composé, procédé pour produire celui-ci, composition de cristaux liquides, et élément électro-optique à cristaux liquides
JPWO2014157551A1 (ja) * 2013-03-29 2017-02-16 Ａｇｃセイミケミカル株式会社 化合物、その製造方法、液晶組成物および液晶電気光学素子
CN113795538A (zh) * 2019-05-10 2021-12-14 索尔维特殊聚合物意大利有限公司 含全氟环丁烷单体的制备方法
US20220194885A1 (en) * 2019-05-10 2022-06-23 Solvay Specialty Polymers Italy S.P.A. Method of making perfluorocyclobutane-containing monomer
US11919834B2 (en) * 2019-05-10 2024-03-05 Solvay Specialty Polymers Italy S.P.A. Method of making perfluorocyclobutane-containing monomer
CN115745750A (zh) * 2022-09-28 2023-03-07 山东天隅新材料科技有限公司 邻苯基苯酚、制备方法及其应用
CN115745750B (zh) * 2022-09-28 2023-12-15 山东天隅新材料科技有限公司 邻苯基苯酚、制备方法及其应用

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